Invention Grant
- Patent Title: Efficient scalable syntheses of abscisic acid, 8′-acetylene abscisic acid and 8′-cyclopropyl abscisic acid
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Application No.: US15241564Application Date: 2016-08-19
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Publication No.: US09725392B2Publication Date: 2017-08-08
- Inventor: Vishal Jheengut , Ken M. Nelson , Suzanne R. Abrams
- Applicant: NATIONAL RESEARCH COUNCIL OF CANADA
- Applicant Address: CA Ottawa, Ontario
- Assignee: NATIONAL RESEARCH COUNCIL OF CANADA
- Current Assignee: NATIONAL RESEARCH COUNCIL OF CANADA
- Current Assignee Address: CA Ottawa, Ontario
- Agency: Bereskin & Parr LLP/S.E.N.C.R.L., s.r.l.
- Agent Patricia Folkins
- Main IPC: C07C51/09
- IPC: C07C51/09 ; C07C46/06 ; C07C67/40 ; C07C67/327 ; C07C403/16

Abstract:
Methods are provided for synthesis of abscisic acid and 8′ analogues thereof (including an enantiopure 8′-acetylene analogue) including methods wherein the previously reported first step of oxidation of 2,6-dimethylphenol (VI) to 2,6-dimethylbenzoquinone, mono ketal (VII) is replaced by a novel two step process comprising (i) oxidation of 2,6-dimethylphenol (VI) using potassium peroxymonosulfate with a catalytic amount of iodobenzene to produce 2,6-dimethylbenzoquinone (XVI) and (ii) ketalization of 2,6-dimethylbenzoquinone (XVI) using ethylene glycol, trimethylorthoformate with a catalytic amount of p-toluenesulfonic acid to produce 2,6-dimethylbenzoquinone, mono ketal (VII).
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